CA2189311A1 - Compositions reticulables renfermant une cycloolefine et une charge - Google Patents

Compositions reticulables renfermant une cycloolefine et une charge

Info

Publication number: CA2189311A1
Authority: CA; Canada
Prior art keywords: component; composition according; substituted; unsubstituted; formula
Prior art date: 1995-11-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002189311A

Other languages

English (en)

Inventor

Frans Setiabudi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF Schweiz AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-11-02

Filing date

1996-10-31

Publication date

1997-05-03

1996-10-31 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1997-05-03 Publication of CA2189311A1 publication Critical patent/CA2189311A1/fr

Status Abandoned legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 66
150000001925 cycloalkenes Chemical class 0.000 title claims abstract description 14
239000000945 filler Substances 0.000 title claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 39
239000003054 catalyst Substances 0.000 claims abstract description 21
229910052799 carbon Inorganic materials 0.000 claims abstract description 20
229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
238000007152 ring opening metathesis polymerisation reaction Methods 0.000 claims abstract description 14
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
229910000077 silane Inorganic materials 0.000 claims abstract description 10
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 9
239000000463 material Substances 0.000 claims abstract description 8
125000006734 (C2-C20) alkoxyalkyl group Chemical group 0.000 claims abstract description 5
125000004429 atom Chemical group 0.000 claims abstract description 5
125000000962 organic group Chemical group 0.000 claims abstract description 4
229910052710 silicon Inorganic materials 0.000 claims abstract description 4
-1 C1-C12alkyl Chemical group 0.000 claims description 131
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 25
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 18
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
235000012239 silicon dioxide Nutrition 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 16
239000003446 ligand Substances 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
238000000034 method Methods 0.000 claims description 14
125000002723 alicyclic group Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 13
229910052751 metal Inorganic materials 0.000 claims description 13
239000002184 metal Substances 0.000 claims description 13
230000008569 process Effects 0.000 claims description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
150000001450 anions Chemical class 0.000 claims description 12
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
125000001072 heteroaryl group Chemical group 0.000 claims description 11
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 10
125000003710 aryl alkyl group Chemical group 0.000 claims description 10
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 10
150000002390 heteroarenes Chemical class 0.000 claims description 9
229910052707 ruthenium Inorganic materials 0.000 claims description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
150000002825 nitriles Chemical class 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 7
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
238000005649 metathesis reaction Methods 0.000 claims description 7
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
229910052681 coesite Inorganic materials 0.000 claims description 6
229910052906 cristobalite Inorganic materials 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000000377 silicon dioxide Substances 0.000 claims description 6
229910052682 stishovite Inorganic materials 0.000 claims description 6
229930192474 thiophene Natural products 0.000 claims description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
229910052905 tridymite Inorganic materials 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
229910052762 osmium Inorganic materials 0.000 claims description 5
229920000642 polymer Polymers 0.000 claims description 5
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 4
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 4
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
125000004475 heteroaralkyl group Chemical group 0.000 claims description 4
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 4
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
229920002554 vinyl polymer Chemical group 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
150000001342 alkaline earth metals Chemical class 0.000 claims description 3
229910052593 corundum Inorganic materials 0.000 claims description 3
125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
229910044991 metal oxide Inorganic materials 0.000 claims description 3
150000004706 metal oxides Chemical class 0.000 claims description 3
LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 claims description 2
QFVYAQIVJUCNSJ-UHFFFAOYSA-N 3,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=CC(S(O)(=O)=O)=C1 QFVYAQIVJUCNSJ-UHFFFAOYSA-N 0.000 claims description 2
RLTPXEAFDJVHSN-UHFFFAOYSA-N 4-(trifluoromethyl)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 RLTPXEAFDJVHSN-UHFFFAOYSA-N 0.000 claims description 2
125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
229910052914 metal silicate Inorganic materials 0.000 claims description 2
230000007935 neutral effect Effects 0.000 claims description 2
JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 2
150000002848 norbornenes Chemical class 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
229910001845 yogo sapphire Inorganic materials 0.000 claims description 2
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 3
125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
229920001296 polysiloxane Polymers 0.000 claims 1
235000013350 formula milk Nutrition 0.000 description 37
239000000843 powder Substances 0.000 description 14
239000010453 quartz Substances 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 6
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
150000004756 silanes Chemical class 0.000 description 6
239000002904 solvent Substances 0.000 description 6
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000001153 fluoro group Chemical group F* 0.000 description 5
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
229920000636 poly(norbornene) polymer Polymers 0.000 description 5
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
241001120493 Arene Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
125000002102 aryl alkyloxo group Chemical group 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 4
229910001868 water Inorganic materials 0.000 description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 3
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
238000005266 casting Methods 0.000 description 3
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
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VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-M phenylacetate Chemical compound [O-]C(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-M 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000000049 pigment Substances 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
238000003672 processing method Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
GYQFZZIOJGPSSR-UHFFFAOYSA-N prop-2-ynylbenzene Chemical compound [C-]#CCC1=CC=CC=C1 GYQFZZIOJGPSSR-UHFFFAOYSA-N 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
229960005335 propanol Drugs 0.000 description 1
NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000010125 resin casting Methods 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 1
NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
FCFMKFHUNDYKEG-UHFFFAOYSA-N thietane 1,1-dioxide Chemical compound O=S1(=O)CCC1 FCFMKFHUNDYKEG-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 1
YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 description 1
239000010456 wollastonite Substances 0.000 description 1
229910052882 wollastonite Inorganic materials 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Compositions Of Macromolecular Compounds (AREA)
Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Inorganic Insulating Materials (AREA)

CA002189311A 1995-11-02 1996-10-31 Compositions reticulables renfermant une cycloolefine et une charge Abandoned CA2189311A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH310895		1995-11-02
CH3108/95		1995-11-02

Publications (1)

Publication Number	Publication Date
CA2189311A1 true CA2189311A1 (fr)	1997-05-03

Family

ID=4248796

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002189311A Abandoned CA2189311A1 (fr)	1995-11-02	1996-10-31	Compositions reticulables renfermant une cycloolefine et une charge

Country Status (5)

Country	Link
US (1)	US6001909A (fr)
EP (1)	EP0771830B1 (fr)
JP (1)	JPH09183833A (fr)
CA (1)	CA2189311A1 (fr)
DE (1)	DE59610089D1 (fr)

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US7994238B2 (en) *	2007-09-04	2011-08-09	General Electric Company	Article and associated method
US8039543B2 (en) *	2007-09-04	2011-10-18	General Electric Company	Composition comprising a coupling agent and a cycloolefin, the coupling agent comprising a reaction product of an epoxy-substituted cycloolefin and an aromatic amine
US7906568B2 (en) *	2007-09-04	2011-03-15	General Electric Company	Coupling agent composition and associated method
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JP7048502B2 (ja)	2016-02-05	2022-04-05	ストラタシスリミテッド	ポリアミド形成材料を使用する三次元インクジェット印刷
EP3411216A4 (fr) *	2016-02-05	2019-07-24	Stratasys Ltd.	Impression 3d à commande numérique à l'aide de la polymérisation par métathèse par ouverture de cycle
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1996
- 1996-10-24 DE DE59610089T patent/DE59610089D1/de not_active Expired - Fee Related
- 1996-10-24 EP EP96810707A patent/EP0771830B1/fr not_active Expired - Lifetime
- 1996-10-28 US US08/736,703 patent/US6001909A/en not_active Expired - Fee Related
- 1996-10-31 CA CA002189311A patent/CA2189311A1/fr not_active Abandoned
- 1996-11-05 JP JP8308706A patent/JPH09183833A/ja not_active Withdrawn

Also Published As

Publication number	Publication date
JPH09183833A (ja)	1997-07-15
EP0771830A3 (fr)	1998-07-22
EP0771830A2 (fr)	1997-05-07
EP0771830B1 (fr)	2003-01-29
US6001909A (en)	1999-12-14
DE59610089D1 (de)	2003-03-06

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Date	Code	Title	Description
2011-04-07	FZDE	Discontinued	Effective date: 20061031

Publication	Publication Date	Title
CA2189311A1 (fr)	1997-05-03	Compositions reticulables renfermant une cycloolefine et une charge
CA2242060A1 (fr)	1999-01-03	Adhesif a base de cycloolefine
US6008306A (en)	1999-12-28	Thermal metathesis polymerization process and a polymerisable composition
AU700258B2 (en)	1998-12-24	Polymerizable compound and a polymerization process
EP0399682B1 (fr)	1995-02-08	Composition d'étanchéité à base de siloxanes à groupes fonctionnels oximo-éthoxy et à durcissement rapide
AU613696B2 (en)	1991-08-08	Organopolysiloxane compositions which can be crosslinked to form elastomers with elimination of alcohols
NZ210695A (en)	1988-05-30	Polyorganosiloxane compositions containing chelated-tin crosslinking catalyst
US4673750A (en)	1987-06-16	Auto-adhering one-component RTV silicone sealant composition utilizing glycidoxyalkyl substituted alkoxy-oxime silane as an adhesion promoter
US5138009A (en)	1992-08-11	Curable compositions comprising organopolysiloxane-polyoxyalkylene block copolymers and cured products obtained from the compositions
CA2205463A1 (fr)	1996-05-30	Monomeres reticulables et compositions et polymeres reticules
US5025048A (en)	1991-06-18	Organosilicon composition comprising stabilizer
US6100323A (en)	2000-08-08	Curable composition comprising a diels-alder-adduct of cyclopentadiene and a filler
US6162883A (en)	2000-12-19	Catalyst mixture and polymerizable composition
US4956436A (en)	1990-09-11	Tin monochelate catalysis of organopolysiloxane compositions
EP0577276B1 (fr)	1997-08-20	Composition élastomère dessiccative à haute résistance
US5349037A (en)	1994-09-20	Adhesive composition
US3922246A (en)	1975-11-25	Organopolysiloxane compositions which cure at ambient temperature
US5922802A (en)	1999-07-13	Thixotropic agent for filled cycloolefins
AU593369B2 (en)	1990-02-08	Compositions which are storable with exclusion of water and crosslink at room temperature to give elastomers when water is admitted
US5240984A (en)	1993-08-31	Silicon rubber composition
KR970007245B1 (ko)	1997-05-07	입체장애 페놀기와 반응기가 함유된 폴리실옥산 안정화제
EP4267659B1 (fr)	2026-03-25	Copolymère de siloxane-imide et composition durcissable par addition le comprenant
JPH0457850A (ja)	1992-02-25	室温硬化性組成物
US5036125A (en)	1991-07-30	Single-component, storage-stable organopolysiloxanes crosslinkable into elastomeric state
EP0551211A1 (fr)	1993-07-14	Composition d'élastomère de silicone fluoré